naphtho[2,3-d][1,3]dioxol-5-yl trifluoromethanesulfonate | 1270093-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphtho[2,3-d][1,3]dioxol-5-yl trifluoromethanesulfonate
• 英文别名: benzo[f][1,3]benzodioxol-5-yl trifluoromethanesulfonate；1-(Trifluoromethanesulfonyloxy)-6,7-(epoxymethanoxy)naphthalene
• CAS: 1270093-14-5
• 化学式: C₁₂H₇F₃O₅S
• 分子量: 320.246
• InChiKey: LVPYOTZNVJIODM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  naphtho[2,3-d][1,3]dioxol-5-yl trifluoromethanesulfonate 在 草酰氯 、 phenanthroline monohydrate 、 palladium diacetate 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-3-(naphtho[2,3-d][1,3]dioxol-5-yl)-N,N-dibutylacrylamide
  参考文献：
  名称：

  Efficient Modulation of γ-Aminobutyric Acid Type A Receptors by Piperine Derivatives

  摘要：

  Piperine activates TRPV1 (transient receptor potential vanilloid type 1 receptor) receptors and modulates gamma-aminobutyric acid type A receptors (GABA(A)R). We have synthesized a library of 76 piperine analogues and analyzed their effects on GABA(A)R by means of a two-microelectrode voltage-clamp technique. GABA(A)R were expressed in Xenopus laevis oocytes. Structure-activity relationships (SARs) were established to identify structural elements essential for efficiency and potency. Efficiency of piperine derivatives was significantly increased by exchanging the piperidine moiety with either N,N-dipropyl, N,N-diisopropyl, N,N-dibutyl, p-methylpiperidine, or N,N-bis(trifluoroethyl) groups. Potency was enhanced by replacing the piperidine moiety by N,N-dibutyl, N,N-diisobutyl, or N,N-bistrifluoroethyl groups. Linker modifications did not substantially enhance the effect on GABA(A)R. Compound 23 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide] induced the strongest modulation of GABA(A) (maximal GABA-induced chloride current modulation (IGABA-max = 1673% +/- 146%, EC50 = 51.7 +/- 9.5 mu M), while 25 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dibutyl-2,4-pentadienamide] displayed the highest potency (EC50 = 13.8 +/- 1.8 mu M, IGABA-max = 760% +/- 47%). Compound 23 induced significantly stronger anxiolysis in mice than piperine and thus may serve as a starting point for developing novel GABA(A)R modulators.

  DOI：

  10.1021/jm5002277
• 作为产物：
  描述：

  5,8-dihydro-5,8-epoxynaphtho[2,3-d]-1,3-dioxole 在 吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 naphtho[2,3-d][1,3]dioxol-5-yl trifluoromethanesulfonate
  参考文献：
  名称：

  钯催化的多米诺骨牌三氟甲磺酸酯的直接芳基化/ N-芳基化反应正式合成亚硝胺和NK109

  摘要：

  由于起始原料的可获得性，在钯催化的多米诺骨牌直接芳基化/ N-芳基化中使用芳基三氟甲磺酸酯作为反应伙伴具有很大的优势。此外，它允许方便地获得生物学上令人感兴趣的苯并[ c ]菲啶生物碱。

  DOI：

  10.1021/ol200174g

文献信息

• Rapid and Convergent Assembly of Natural Benzo[c]phenanthridines by Palladium/Norbornene Catalysis
  作者：Max Malacria、Giovanni Maestri、Pierre-Alexandre Deyris、Tatiana Caneque-Cobo、Filipe Gomes、Vanessa Narbonne

  DOI：10.3987/com-13-s(s)62

  日期：——

  construction of cyclic scaffolds is based on the use of reagents possessing a suitably tethered (masked) nucleophile which could terminate the catalytic cycle by reacting with an electrophilic organopalladium(II) intermediate. In this context, the association of a palladium salt with norbornene delivers a remarkable catalytic system that allows the multiple functionalization of an aryl halide in one pot. After

  描述了一小部分天然苯并[c]菲啶的直接全合成。通过钯/降冰片烯联合催化和顺序转移氢化，三氟甲磺酸芳基酯与溴苄胺的选择性偶联将这些生物碱一锅法输送。最初形成的二氢菲啶可以顺利脱氢，而降冰片烯既可以作为它们组装的催化剂，也可以作为它们脱氢过程中的牺牲烯烃。钯催化是有机化学的有力工具，并且由于其多功能性而在合成中得到广泛应用。通过使用现成的底物，在过去的二十年中报道了许多选择性形成 C-C 和 C-杂原子键的方案。构建环状支架的一个强有力的策略是基于使用具有适当束缚（掩蔽）亲核试剂的试剂，该试剂可以通过与亲电子有机钯 (II) 中间体反应来终止催化循环。在这种情况下，钯盐与降冰片烯的结合提供了一个显着的催化体系，可以在一锅中对芳基卤化物进行多重官能化。在 Catellani 的开创性工作之后，报告了许多合成应用，它们采用这种策略提供了复杂的多环支架。在氮杂环的背景下，已经报道了提供咔唑、菲啶或二
• CARBONIC ANHYDRASE ENZYME INHIBITORS AND METHODS OF USE THEREOF
  申请人：[en]RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY

  公开号：WO2024124023A2

  公开（公告）日：2024-06-13

  Provided herein are novel compounds, such as a compound of Formula I or Formula A: or a salt thereof, wherein R1-R3, L1, R10, ring A and ring B have any of the values described in the specification, as well as compositions comprising the novel compounds herein. The compounds are typically carbonic anhydrase inhibitors and are useful for the prophylactic or therapeutic treatment of a disease or condition mediated by a carbonic anhydrase enzyme.
• Efficient Modulation of γ-Aminobutyric Acid Type A Receptors by Piperine Derivatives
  作者：Angela Schöffmann、Laurin Wimmer、Daria Goldmann、Sophia Khom、Juliane Hintersteiner、Igor Baburin、Thomas Schwarz、Michael Hintersteininger、Peter Pakfeifer、Mouhssin Oufir、Matthias Hamburger、Thomas Erker、Gerhard F. Ecker、Marko D. Mihovilovic、Steffen Hering

  DOI：10.1021/jm5002277

  日期：2014.7.10

  Piperine activates TRPV1 (transient receptor potential vanilloid type 1 receptor) receptors and modulates gamma-aminobutyric acid type A receptors (GABA(A)R). We have synthesized a library of 76 piperine analogues and analyzed their effects on GABA(A)R by means of a two-microelectrode voltage-clamp technique. GABA(A)R were expressed in Xenopus laevis oocytes. Structure-activity relationships (SARs) were established to identify structural elements essential for efficiency and potency. Efficiency of piperine derivatives was significantly increased by exchanging the piperidine moiety with either N,N-dipropyl, N,N-diisopropyl, N,N-dibutyl, p-methylpiperidine, or N,N-bis(trifluoroethyl) groups. Potency was enhanced by replacing the piperidine moiety by N,N-dibutyl, N,N-diisobutyl, or N,N-bistrifluoroethyl groups. Linker modifications did not substantially enhance the effect on GABA(A)R. Compound 23 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide] induced the strongest modulation of GABA(A) (maximal GABA-induced chloride current modulation (IGABA-max = 1673% +/- 146%, EC50 = 51.7 +/- 9.5 mu M), while 25 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dibutyl-2,4-pentadienamide] displayed the highest potency (EC50 = 13.8 +/- 1.8 mu M, IGABA-max = 760% +/- 47%). Compound 23 induced significantly stronger anxiolysis in mice than piperine and thus may serve as a starting point for developing novel GABA(A)R modulators.
• Formal Synthesis of Nitidine and NK109 via Palladium-Catalyzed Domino Direct Arylation/<i>N</i>-Arylation of Aryl Triflates
  作者：Mathieu Blanchot、David A. Candito、Florent Larnaud、Mark Lautens

  DOI：10.1021/ol200174g

  日期：2011.3.18

  The use of aryl triflates as reaction partners in a palladium-catalyzed domino direct arylation/N-arylation provides a great advantage due to the availability of starting materials. Furthermore, it allows expedient access to biologically interesting benzo[c]phenanthridine alkaloids.

  由于起始原料的可获得性，在钯催化的多米诺骨牌直接芳基化/ N-芳基化中使用芳基三氟甲磺酸酯作为反应伙伴具有很大的优势。此外，它允许方便地获得生物学上令人感兴趣的苯并[ c ]菲啶生物碱。